5-Aminoisoquinoline → N-[1-(4-chlorophenyl)-1-methylethyl]-N'-5-isoquinolinylurea

HRID 887211Notes

Reaction equation

HRID 887211 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:22]=[C:23]=[O:24])([CH3:21])[CH3:20])=[CH:15][CH:14]=1>C1COCC1>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([NH:22][C:23]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]=[CH:7]3)=[O:24])([CH3:21])[CH3:20])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 707665-AminoisoquinolineHCID 131183231-Chloro-4-(2-isocyanatopropan-2-yl)benzene

Product 1

HCID 10404960N-[1-(4-chlorophenyl)-1-methylethyl]-N'-5-isoquinolinylureaYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared using 5-aminoisoquinoline, the product of Example 76B and the procedure described in Example 73B except that THF was used as solvent. The product was recrystallized from ethyl acetate to provide the title compound as a white solid (840 mg, 34%). MS (ESI+) m/z 355 (M+H)+; MS (ESI−) m/z 353 (M−H)−; 1H NMR (DMSO-d6, 300 MHz) δ 1.63 (s, 6H), 7.23 (s, 1H), 7.37 (d, J 8.8, 2H), 7.47 (d, J 8.8, 2H), 7.73 (t, J 9.2, 1H), 7.93 (d, J 8.1, 1H), 8.25 (d, J 6.4, 1H), 8.39 (d, J 8.1, 1H), 8.67 (d, J 6.4, 1H), 8.87 (s, 1H), 9.58 (s, 1H); Anal. Calcd for C19H18ClN3O HCl 0.25EtOH: C, 60.40; H, 5.33; N, 10.54. Found: C, 60.82; H, 5.23; N, 10.45.

Workup

  1. customThe title compound was prepared
  2. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-dcaa1be967e54703bc01983d30d30517
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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